A Simple and Efficient Synthesis of Functionalized Cyclic Carbonate Monomers Using a Versatile Pentafluorophenyl Ester Intermediate

An improved two-step synthetic route to functionalized cyclic carbonate monomers that features a novel cyclic carbonate intermediate with an active pentafluorophenyl ester group (MTC-OPhF5) has been developed. The versatile pentafluorophenyl ester intermediate can be synthesized on the gram to kilog...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2010-10, Vol.132 (42), p.14724-14726
Main Authors: Sanders, Daniel P, Fukushima, Kazuki, Coady, Daniel J, Nelson, Alshakim, Fujiwara, Masaki, Yasumoto, Manabu, Hedrick, James L
Format: Article
Language:English
Subjects:
Carbonates - chemical synthesis
Carbonates - chemistry
Cyclization
Esters
Fluorobenzenes - chemistry
Phenols - chemistry
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Summary:An improved two-step synthetic route to functionalized cyclic carbonate monomers that features a novel cyclic carbonate intermediate with an active pentafluorophenyl ester group (MTC-OPhF5) has been developed. The versatile pentafluorophenyl ester intermediate can be synthesized on the gram to kilogram scale in one high-yielding step and is easy to store and handle on the benchtop. The active pentafluorophenyl ester of MTC-OPhF5 is amenable to further substitution with suitable nucleophiles such as alcohols and amines to generate functionalized cyclic carbonates in high yields. The substitution reaction is tolerant of a wide variety of functionalities, including various hydrophobic and hydrophilic groups, reactive functionalities (via thiol−ene click chemistry or alkyl halides), and protected acids, alcohols, thiols, and amines. In view of the ever-increasing need for biodegradable and biocompatible polymers, this new methodology provides a simple and versatile platform for the synthesis of new and innovative materials.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja105332k